6 Shoes to Wear with Denim Maxi Skirts to Impress All Your Fashion Friends

My absolute favorite way to style a denim maxi (or midi) skirt is with a sleek knee-high boot. They are a match made in heaven, especially in colder months when you want to keep your legs warm without resorting to pants. Almost any style will do here—flat moto boots, rain-proof Wellies, burgundy stilettos—but my go-to is usually a pointy-toe boot with a block heel, for the ideal combination of fashion and function.

No shade to Gen Z here, but this is one instance in which no-show socks are a must for two simple reasons. The first is the One Palm Rule for pairing sneakers with maxi skirts, which suggests there should be at least one palm width between the top of your sneaker and the hem of your dress. Showing a bit of leg, even if it’s just a few inches, helps maintain a sense of your figure and lighten your look, especially if you’re wearing heavy denim. But let’s say you’re wearing a midi and not a maxi. In that case, adding a scrunched calf sock ends up reading super ‘80s, and not necessarily in the best way.

Contrary to my advice above, boots can have much more overlap with or distance from the hem of your skirt. This is why I don’t recommend pairing a low ankle boot with a denim maxi or midi. The proportions wind up just looking odd, whereas a higher-cut boot—even one that ends right above the ankle bone—looks more intentional, no matter the length of your skirt.

Closed-toe heels and maxi skirts, of just about any style, are yet another tried-and-true duo. You don’t even need to go particularly high with the heel, just an inch or two is fine. And while I prefer the leg-lengthening effects of a sleek pointed toe, you could just as easily rock an almond, square or rounded toe, if those are more your style.

For a more walkable option, try a trendy ballet, Mary Jane or pointy-toe flat. They work beautifully with skirts of any length, from mini all the way down to an ankle-covering maxi. However if you do opt for a very long silhouette or a denim skirt with a bit more volume around the ankles, I highly suggest choosing a pair of flats designed to pop, like super-bright colors, flats with an embellishment on the toe or a pointy-toe silhouette. This will help ensure your feet don’t get swallowed by all that denim.

Earlier I mentioned closed-toe heels as a great shoe to wear with denim skirts, but the same is not true for heeled sandals. Often the disparity between a strappy minimalist shoe and a heavy denim maxi is just too much. Their vibes (sexy, party shoe vs. western-inspired skirt) are just too different. However, if you cut the heel and opt for a flat sandal instead, suddenly your ‘fit looks much more cohesive. This is especially true if you sandwich your denim maxi between a casual summery shirt and sandal.